Vepreva Anastasia, Bunev Alexander S, Kudinov Andrey Yu, Kantin Grigory, Krasavin Mikhail, Dar'in Dmitry
Saint Petersburg State University, Saint Petersburg 199034, Russian Federation.
Medicinal Chemistry Center, Togliatti State University, 445020 Togliatti, Russian Federation.
Beilstein J Org Chem. 2022 May 11;18:533-538. doi: 10.3762/bjoc.18.55. eCollection 2022.
Formation of unusual unsymmetrical dimers or/and indenes via Rh(esp)-catalyzed decomposition of 3-diazo-2-arylidenesuccinimides has been investigated. The reaction proceeded under mild conditions, and its result was shown to strongly depend on the nature of the substituents in the diazo substrate. The new reaction provides access to dibenzoazulenodipyrrole and indenopyrrole derivatives in moderate to high yield. Dibenzoazulenodipyrroles bearing alkyl substituents at the nitrogen atom showed pronounced cytotoxocity against the A549 human lung adenocarcinoma cell line while -aryl analogs were non-cytotoxic.
通过Rh(esp)催化3-重氮-2-亚芳基琥珀酰亚胺的分解形成不寻常的不对称二聚体或/和茚的反应已被研究。该反应在温和条件下进行，结果表明其强烈依赖于重氮底物中取代基的性质。该新反应能以中等至高收率得到二苯并薁并二吡咯和茚并吡咯衍生物。在氮原子上带有烷基取代基的二苯并薁并二吡咯对A549人肺腺癌细胞系显示出明显的细胞毒性，而芳基类似物则无细胞毒性。
